Synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues through a common synthetic route

Chem Phys Lipids. 2004 Jul;130(2):117-26. doi: 10.1016/j.chemphyslip.2004.02.008.

Abstract

Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arachidonate 15-Lipoxygenase / metabolism
  • Arachidonic Acid / chemical synthesis*
  • Arachidonic Acid / chemistry*
  • Arachidonic Acid / metabolism
  • Glycine max / enzymology
  • Kinetics
  • Molecular Structure
  • Oxidation-Reduction
  • Rabbits
  • Reticulocytes / enzymology

Substances

  • Arachidonic Acid
  • Arachidonate 15-Lipoxygenase